organic papers

o2378 Burcu Arslan et al. � C54H70O4 doi:10.1107/S1600536804029617 Acta Cryst. (2004). E60, o2378±o2379

Acta Crystallographica Section E

Structure ReportsOnline

ISSN 1600-5368

1,2,4,5-Tetrakis(2-tert-butyl-4-methylphenoxy-methyl)benzene

Burcu Arslan,a* Canan Kazak,a

Nesuhi Akdemir,b Cihan Kantarb

and Erbil AgÆarb

aDepartment of Physics, Ondokuz Mayõs

University, TR-55139 Samsun, Turkey, andbDepartment of Chemistry, Ondokuz Mayõs

University, TR-55139 Samsun, Turkey

Correspondence e-mail: nbarslan@ttnet.net.tr

Key indicators

Single-crystal X-ray study

T = 293 K

Mean �(C±C) = 0.005 AÊ

R factor = 0.072

wR factor = 0.161

Data-to-parameter ratio = 17.6

For details of how these key indicators were

automatically derived from the article, see

http://journals.iucr.org/e.

# 2004 International Union of Crystallography

Printed in Great Britain ± all rights reserved

The centrosymmetric title compound, C54H70O4, contains a

benzene ring at the centre and four 2-tert-butyl-4-methyl-

phenoxymethyl substituents. In the structure of the molecule,

some of the benzene rings are coplanar. The title compound

displays intramolecular CÐH� � �O hydrogen bonds. The

crystal structure is stabilized by CÐH� � �� interactions.

Comment

1,2,4,5-Tetrakis(2-tert-butyl-4-methylphenoxymethyl)benzene,

(I), and similar compounds are generally used for the synthesis

of polystyrene polymers. These polymers have become of

interest in recent years because of their unique properties and

important applications (Kuriyama & Otsu, 1984; Kwon et al.,

2003).

The structure of the centrosymmetric molecule consists of a

benzene ring (ring A, C13±C27) at the centre with four 2-tert-

butyl-4-methylphenoxymethyl substituents at C13, C13i, C14

and C14i [Fig. 1; symmetry code: (i)ÿx, 1 ÿ y, 1 ÿ z.] Rings A

and B (C1±C6) are coplanar. Atom C26 attached to ring C

(C16±C21) has a larger displacement parameter than usual.

The torsion angles C1ÐO1ÐC12ÐC13 (between rings A and

B) and C14ÐC15ÐO2ÐC16 (between rings A and C) are

179.0 (2) and 93.2 (3)�, respectively. The CÐO bond lengths

are in the range 1.378 (3)±1.434 (3)� (Table 1). The crystal

structure of the title compound is stabilized by CÐH� � ��interactions and there are also weak intramolecular CÐH� � �Ointeractions (Table 2).

Experimental

A solution of 2-tert-butyl-4-methylphenol (1.48 g, 9.01 mmol) and

K2CO3 (2.5 g, 18.12 mmol) in dry dimethylformamide (DMF, 50 ml)

was heated and stirred at 313 K under N2 for 1 h. To this mixture, a

solution of 1,2,4,5-tetrakis(bromomethyl)benzene (1.00 g, 2.22 mmol)

in dry DMF (20 ml) was added dropwise under N2 over a period of 2±

3 h. The reaction mixture was stirred for 2 d at 313 K and poured into

iced water (150 g). The product was ®ltered off and washed with

(10% w/w) NaOH solution and water until the ®ltrate was neutral.

Recrystallization from an ethanol solution gave a white product

(yield 0.06 g, 3.45%). Single crystals were obtained from absolute

ethanol at room temperature via slow evaporation (m.p. 406 K);

Received 26 October 2004

Accepted 15 November 2004

Online 20 November 2004

elemental analysis calculated for C54H70O4: C 82.82, H 9.01%; found:

C 82.92, H 9.10%.

Crystal data

C54H70O4

Mr = 783.10Monoclinic, P21=na = 10.1833 (9) AÊ

b = 21.5350 (16) AÊ

c = 11.5029 (11) AÊ

� = 107.725 (7)�

V = 2402.8 (4) AÊ 3

Z = 2

Dx = 1.082 Mg mÿ3

Mo K� radiationCell parameters from 23 574

re¯ections� = 1.9±28.8�

� = 0.07 mmÿ1

T = 293 (2) KPrism, colourless0.40 � 0.22 � 0.04 mm

Data collection

Stoe IPDS-2 diffractometer! scansAbsorption correction: by

integration (X-RED32;Stoe & Cie, 2002)Tmin = 0.983, Tmax = 0.997

24 464 measured re¯ections

4725 independent re¯ections2611 re¯ections with I > 2�(I)Rint = 0.092�max = 26.0�

h = ÿ12! 12k = ÿ26! 26l = ÿ14! 14

Refinement

Re®nement on F 2

R[F 2 > 2�(F 2)] = 0.072wR(F 2) = 0.161S = 1.044725 re¯ections268 parametersH-atom parameters constrained

w = 1/[�2(Fo2) + (0.0548P)2

+ 0.7513P]where P = (Fo

2 + 2Fc2)/3

(�/�)max = 0.009��max = 0.17 e AÊ ÿ3

��min = ÿ0.19 e AÊ ÿ3

Table 1Selected geometric parameters (AÊ , �).

O1ÐC1 1.378 (3)O1ÐC12 1.425 (3)

O2ÐC16 1.383 (4)O2ÐC15 1.433 (3)

C1ÐO1ÐC12ÐC13 179.0 (2) C16ÐO2ÐC15ÐC14 93.2 (3)

Table 2Hydrogen-bonding geometry (AÊ , �).

DÐH� � �A DÐH H� � �A D� � �A DÐH� � �A

C9ÐH9B� � �O1 0.96 2.38 3.012 (4) 123C10ÐH10C� � �O1 0.96 2.31 2.956 (4) 124C12ÐH12A� � �O2 0.97 2.39 2.920 (3) 114C24ÐH24A� � �O2 0.96 2.32 2.953 (5) 123C25ÐH25C� � �O2 0.96 2.39 3.012 (5) 123C27ÐH27� � �O1 0.93 2.36 2.726 (4) 103C12ÐH12B� � �Cg1ii 0.97 2.75 3.572 (3) 143

Symmetry code: (ii) 1ÿ x; 1ÿ y; 1ÿ z. Cg1 is the centroid of ring C (C16±C21).

All H atoms were re®ned using a riding model, with CÐH = 0.93

(aromatic H), 0.97 (methylene H) or 0.96 AÊ (methyl H).

Uiso(aromatic and methylene H) values were set at 1.2Ueq(C), while

Uiso(methyl H) values were set at 1.5Ueq(C).

Data collection: X-AREA (Stoe & Cie, 2002); cell re®nement:

X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s)

used to solve structure: SHELXS97 (Sheldrick, 1997); program(s)

used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular

graphics: ORTEP-3 (Farrugia, 1997); software used to prepare

material for publication: WinGX (Farrugia, 1999).

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837±838.Kuriyama, A. & Otsu, T. (1984). Polym. J. 16, 511±514.Kwon, T. S., Takagi, K., Kunisada, H. & Yuki, Y. (2003). Eur. Polym. J. 39,

1437±1441.Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of

GoÈ ttingen, Germany.Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.

organic papers

Acta Cryst. (2004). E60, o2378±o2379 Burcu Arslan et al. � C54H70O4 o2379

Figure 1An ORTEP-3 (Farrugia, 1997) view of the title compound, showing theatom-numbering scheme, 50% probability displacement ellipsoids andintramolecular hydrogen bonds. [Symmetry code: (i) ÿx, 1 ÿ y, 1 ÿ z.]